EMBL-EBI | Chemical Biology | ChEBI

Example searches: iron*, InChI=1S/CH4O/c1-2/h2H,1H3, caffeine | Advanced Search

CHEBI:183051 - tetraacetyl-N-azidoacetyl-D-mannosamine

ChEBI IDCHEBI:183051
ChEBI Nametetraacetyl-N-azidoacetyl-D-mannosamine
Stars
ASCII Nametetraacetyl-N-azidoacetyl-D-mannosamine
DefinitionA monosaccharide derivative that is D-mannosamine in pyranose form with an azidocarbonyl group substituted on nitrogen and all hydroxy groups acetylated. It can be used to introduce an azido group in living cells which can be metabolized to N-azido acetylneuramic acid and eventually incorporated into the glycoproteins and glycolipids on the cell surface, while exhibiting very low toxicity.
Last Modified22 October 2021
SubmitterMarcus Ennis
DownloadsMolfile
FormulaC15H20N4O10
Net Charge0
Average Mass416.343
Monoisotopic Mass416.11794
SMILESCC(=O)OC[C@H]1OC(OC(C)=O)[C@@H](NC(=O)N=[N+]=[N-])[C@@H](OC(C)=O)[C@@H]1OC(C)=O
InChIInChI=1S/C15H20N4O10/c1-6(20)25-5-10-12(26-7(2)21)13(27-8(3)22)11(17-15(24)18-19-16)14(29-10)28-9(4)23/h10-14H,5H2,1-4H3,(H,17,24)/t10-,11+,12-,13-,14?/m1/s1
InChIKeyMRRKYEUMMAEYHG-DYPLGBCKSA-N
Roles Classification
Biological Role:
immunogen  An antigen capable, on its own, of inducing an immune response.
ChEBI Ontology
Outgoing Relation(s)
tetraacetyl-N-azidoacetyl-D-mannosamine (CHEBI:183051) has functional parent D-mannosamine (CHEBI:62324)
tetraacetyl-N-azidoacetyl-D-mannosamine (CHEBI:183051) has role immunogen (CHEBI:60816)
tetraacetyl-N-azidoacetyl-D-mannosamine (CHEBI:183051) is a acetate ester (CHEBI:47622)
tetraacetyl-N-azidoacetyl-D-mannosamine (CHEBI:183051) is a azide (CHEBI:22680)
tetraacetyl-N-azidoacetyl-D-mannosamine (CHEBI:183051) is a monosaccharide derivative (CHEBI:63367)
IUPAC Name 
1,3,4,6-tetra-O-acetyl-2-[(azidocarbonyl)amino]-2-deoxy-D-mannopyranose
Synonyms  Source
AC4ManNAzChEBI
2-[(azidocarbonyl)amino]-2-deoxy-D-mannopyranose 1,3,4,6-tetraacetateChEBI
Citations